Use the pKa Slide Rule in P. Gilli, L. Pretto, V. Bertolasi, G. Gilli, Acc. Chem. Res. ,...

Use the pKa Slide Rule in P. Gilli, L. Pretto, V. Bertolasi, G. Gilli, Acc. Chem. Res. , 2009 , 42 , 33 to answer these questions:

a. Which forms a stronger hydrogen bond with water, HCN or HSCN?

b. Identify two inorganic acids that are predicted to form strong hydrogen bonds with organic nitriles.

c. Which organic acid in the Slide Rule is predicted to form the strongest hydrogen bond to organic sulfides?

d. Water is a prototypical hydrogen bond donor. Classify the strengths of hydrogen bonds (for example, as strong, medium strong, medium, medium weak, or weak) with the following classes of acceptors: amines, triphosphines, sulfoxides, ketones, and nitro compounds.